6627-65-2

Basic information

• Product Name: 2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one
• Synonyms: 2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one;4(1H)-Pyrimidinone, 2-amino-6-hydroxy-5-methyl- (9CI);2-Amino-6-hydroxy-5-methylpyrimidin-4(1H)-one;Einecs 229-597-8
• CAS NO: 6627-65-2
• Molecular Formula: C₅H₇N₃O₂
• Molecular Weight: 141.12798
• EINECS: 229-597-8
• Product Categories: PYRIMIDINE
• Mol File: 6627-65-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 478.1°Cat760mmHg
• Flash Point: 242.9°C
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 2.78E-08mmHg at 25°C
• Refractive Index: 1.754
• PKA: 7.92±0.10(Predicted)
• CAS DataBase Reference: 2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one(6627-65-2)
• EPA Substance Registry System: 2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one(6627-65-2)

Safety Data

• Hazardous Substances Data: 6627-65-2(Hazardous Substances Data)

Usage

General Description

2-amino-6-hydroxy-5-methyl-1H-pyrimidin-4-one, also known as methyluracil, is a heterocyclic compound with the molecular formula C5H6N2O2. It is a derivative of uracil, an important component of nucleic acids. Methyluracil has been identified as a potent antioxidant and has potential applications in pharmaceuticals and as a supplement in cosmetic products. It has been studied for its potential role in the treatment of inflammatory conditions, as well as for its potential to promote wound healing. Additionally, it has been investigated for its potential to protect against radiation-induced damage. Methyluracil is an important compound with diverse potential applications across various fields.

InChI:InChI=1/C14H9NO2S2/c16-13-12(8-10-6-7-18-9-10)19-14(17)15(13)11-4-2-1-3-5-11/h1-9H/b12-8-

Upstream product

• 50-01-1 guanidine hydrochloride 
• 609-08-5 Diethyl methylmalonate 

Downstream Products

• 7153-13-1 4,6-dichloro-5-methylpyrimidin-2-amine 

Relevant articles and documents

5-substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino- 4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6- dichloropyrimidine with an IC50 of 2 μM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 l M. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF

The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙